[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes

• DOI: 10.1021/acs.orglett.5b01994
• Publication Date: 2015-08-07T12:26:22Z
• Authors: Ting-Ting Zeng; Jun Xuan; Wei Ding; Kuan Wang; Liang-Qiu Lu; Wen-Jing Xiao
• Keywords: Aromatization; Photoredox catalysis; Sequence (biology)

A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis cyclooxygenase-2 inhibitor as well success employing electron-deficient alkenes imines partners.